ES2209113T3 - Heteroligando. - Google Patents

Heteroligando.

Info

Publication number: ES2209113T3
Authority: ES; Spain
Prior art keywords: group; radicals; heterocycle; polymerization; catalyst
Prior art date: 1997-03-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES98905188T

Other languages

English (en)

Spanish (es)

Inventor

Rupert Edward Von Haken Spence

Xiaoliang Gao

Linda Koch

Stephen John Brown

Daryll G. Harrison

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nova Chemicals International SA

Original Assignee

Nova Chemicals International SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-03-19

Filing date

1998-02-27

Publication date

2004-06-16

1998-02-27 Application filed by Nova Chemicals International SA filed Critical Nova Chemicals International SA

2004-06-16 Application granted granted Critical

2004-06-16 Publication of ES2209113T3 publication Critical patent/ES2209113T3/es

2018-02-27 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 claims abstract description 65
238000006116 polymerization reaction Methods 0.000 claims abstract description 47
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 40
239000003446 ligand Substances 0.000 claims abstract description 32
125000002524 organometallic group Chemical group 0.000 claims abstract description 25
150000001336 alkenes Chemical class 0.000 claims abstract description 22
125000001424 substituent group Chemical group 0.000 claims abstract description 14
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 10
239000010936 titanium Substances 0.000 claims description 29
-1 chlorodimethylsilyl Chemical group 0.000 claims description 21
125000005842 heteroatom Chemical group 0.000 claims description 16
125000004429 atom Chemical group 0.000 claims description 15
229910052751 metal Inorganic materials 0.000 claims description 13
239000002184 metal Substances 0.000 claims description 13
229910052719 titanium Inorganic materials 0.000 claims description 12
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 10
150000001450 anions Chemical class 0.000 claims description 9
239000002685 polymerization catalyst Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
229910052698 phosphorus Inorganic materials 0.000 claims description 8
229910052726 zirconium Inorganic materials 0.000 claims description 8
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 7
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 7
229910052752 metalloid Inorganic materials 0.000 claims description 7
150000002738 metalloids Chemical group 0.000 claims description 7
229910052718 tin Inorganic materials 0.000 claims description 7
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
DOWYLTKHRAPLBQ-UHFFFAOYSA-N ClC=1P(C(=C(C1C)C)C)(C1=CC=CC=C1)[SiH](C)C Chemical compound ClC=1P(C(=C(C1C)C)C)(C1=CC=CC=C1)[SiH](C)C DOWYLTKHRAPLBQ-UHFFFAOYSA-N 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
229910052732 germanium Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
230000000737 periodic effect Effects 0.000 claims description 3
229910052710 silicon Inorganic materials 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
229910052787 antimony Inorganic materials 0.000 claims description 2
229910052785 arsenic Inorganic materials 0.000 claims description 2
229910052797 bismuth Inorganic materials 0.000 claims description 2
125000006309 butyl amino group Chemical group 0.000 claims description 2
229910052735 hafnium Inorganic materials 0.000 claims description 2
150000007517 lewis acids Chemical group 0.000 claims description 2
125000003367 polycyclic group Chemical group 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
230000003213 activating effect Effects 0.000 claims 2
239000002841 Lewis acid Substances 0.000 claims 1
239000002585 base Substances 0.000 claims 1
150000007527 lewis bases Chemical group 0.000 claims 1
125000001302 tertiary amino group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 25
238000000034 method Methods 0.000 abstract description 23
229920000092 linear low density polyethylene Polymers 0.000 abstract description 4
239000004707 linear low-density polyethylene Substances 0.000 abstract description 4
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 43
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 42
239000005977 Ethylene Substances 0.000 description 42
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
230000000052 comparative effect Effects 0.000 description 16
229920000642 polymer Polymers 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 13
239000007789 gas Substances 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
239000004698 Polyethylene Substances 0.000 description 9
238000005227 gel permeation chromatography Methods 0.000 description 9
239000000178 monomer Substances 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 7
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
239000012190 activator Substances 0.000 description 6
229920000573 polyethylene Polymers 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
DJMUYABFXCIYSC-UHFFFAOYSA-N 1H-phosphole Chemical compound C=1C=CPC=1 DJMUYABFXCIYSC-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000010528 free radical solution polymerization reaction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical group C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229910007926 ZrCl Inorganic materials 0.000 description 3
230000004913 activation Effects 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000013078 crystal Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
239000012968 metallocene catalyst Substances 0.000 description 3
231100000614 poison Toxicity 0.000 description 3
239000002574 poison Substances 0.000 description 3
238000010557 suspension polymerization reaction Methods 0.000 description 3
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
235000019502 Orange oil Nutrition 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
125000005626 carbonium group Chemical group 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012634 fragment Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
WHJJIUOTIQYMDZ-UHFFFAOYSA-N heptane tris(2-methylpropyl)alumane Chemical compound CCCCCCC.CC(C)C[Al](CC(C)C)CC(C)C WHJJIUOTIQYMDZ-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
DMLLRJGUHDBUPT-UHFFFAOYSA-N n-[dimethyl-(3,4,5-trimethyl-1-phenylphosphol-2-yl)silyl]-2-methylpropan-2-amine Chemical compound CC1=C(C)C(C)=C([Si](C)(C)NC(C)(C)C)P1C1=CC=CC=C1 DMLLRJGUHDBUPT-UHFFFAOYSA-N 0.000 description 2
239000010502 orange oil Substances 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 2
230000007704 transition Effects 0.000 description 2
239000003039 volatile agent Substances 0.000 description 2
LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 1
YXFVVABEGXRONW-UICOGKGYSA-N 1-deuterio-2-methylbenzene Chemical compound [2H]C1=CC=CC=C1C YXFVVABEGXRONW-UICOGKGYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XJONFIGVOQMBIP-UHFFFAOYSA-L Cl[Zr](Cl)C1C=CC=C1 Chemical compound Cl[Zr](Cl)C1C=CC=C1 XJONFIGVOQMBIP-UHFFFAOYSA-L 0.000 description 1
229920003189 Nylon 4,6 Polymers 0.000 description 1
KODWHVAQXOBMRJ-UHFFFAOYSA-N P1C(=CC=C1)[Ti] Chemical compound P1C(=CC=C1)[Ti] KODWHVAQXOBMRJ-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
229910007928 ZrCl2 Inorganic materials 0.000 description 1
JFWBIRAGFWPMTI-UHFFFAOYSA-N [Zr].[CH]1C=CC=C1 Chemical compound [Zr].[CH]1C=CC=C1 JFWBIRAGFWPMTI-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical class CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
239000003999 initiator Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 description 1
QBNOPZJAURRQCE-UHFFFAOYSA-M magnesium;prop-1-yne;bromide Chemical compound [Mg+2].[Br-].CC#[C-] QBNOPZJAURRQCE-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000003947 neutron activation analysis Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
150000004857 phospholes Chemical class 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
150000003967 siloles Chemical class 0.000 description 1
125000005353 silylalkyl group Chemical group 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
238000012546 transfer Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002435 venom Substances 0.000 description 1
231100000611 venom Toxicity 0.000 description 1
210000001048 venom Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/02—Ethene
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S106/00—Compositions: coating or plastic
- Y10S106/901—Low molecular weight hydrocarbon polymer-containing mixture

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

ES98905188T 1997-03-19 1998-02-27 Heteroligando. Expired - Lifetime ES2209113T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA002200373A CA2200373C (fr)	1997-03-19	1997-03-19	Heteroligand
CA2200373		1997-03-19

Publications (1)

Publication Number	Publication Date
ES2209113T3 true ES2209113T3 (es)	2004-06-16

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ID=4160202

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES98905188T Expired - Lifetime ES2209113T3 (es)	1997-03-19	1998-02-27	Heteroligando.

Country Status (8)

Country	Link
US (1)	US6124487A (fr)
EP (1)	EP0971942B1 (fr)
AT (1)	ATE251635T1 (fr)
AU (1)	AU6086498A (fr)
CA (1)	CA2200373C (fr)
DE (1)	DE69818810T2 (fr)
ES (1)	ES2209113T3 (fr)
WO (1)	WO1998041529A1 (fr)

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1997
- 1997-03-19 CA CA002200373A patent/CA2200373C/fr not_active Expired - Fee Related
1998
- 1998-02-27 AT AT98905188T patent/ATE251635T1/de not_active IP Right Cessation
- 1998-02-27 WO PCT/CA1998/000166 patent/WO1998041529A1/fr not_active Ceased
- 1998-02-27 EP EP98905188A patent/EP0971942B1/fr not_active Expired - Lifetime
- 1998-02-27 ES ES98905188T patent/ES2209113T3/es not_active Expired - Lifetime
- 1998-02-27 DE DE69818810T patent/DE69818810T2/de not_active Expired - Fee Related
- 1998-02-27 AU AU60864/98A patent/AU6086498A/en not_active Abandoned
- 1998-03-06 US US09/036,241 patent/US6124487A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2200373A1 (fr)	1998-09-19
EP0971942A1 (fr)	2000-01-19
US6124487A (en)	2000-09-26
DE69818810T2 (de)	2004-08-05
WO1998041529A1 (fr)	1998-09-24
EP0971942B1 (fr)	2003-10-08
DE69818810D1 (en)	2003-11-13
CA2200373C (fr)	2005-11-15
AU6086498A (en)	1998-10-12
ATE251635T1 (de)	2003-10-15

Publication	Publication Date	Title
ES2209113T3 (es)	2004-06-16	Heteroligando.
RU2169735C2 (ru)	2001-06-27	КАТАЛИТИЧЕСКАЯ СИСТЕМА, СПОСОБ ПОЛИМЕРИЗАЦИИ ЭТИЛЕНА И СПОСОБ ПОЛИМЕРИЗАЦИИ ЛИНЕЙНЫХ ИЛИ РАЗВЕТВЛЕННЫХ α-ОЛЕФИНОВ
US5096867A (en)	1992-03-17	Monocyclopentadienyl transition metal olefin polymerization catalysts
EP0420436B1 (fr)	1996-08-14	Catalyseurs pour la polymérisation d'oléfines
US6051667A (en)	2000-04-18	Olefin polymerization using a catalyst having a bridged cyclopentadienyl-phosphole ligand
US5631391A (en)	1997-05-20	Monocyclopentadienyl titanium metal compounds for ethylene-α-olefin-copolymer production catalysts
ES2225761T3 (es)	2005-03-16	Catalizadores biometalicos para la polimerizacion de olefinas.
KR19990008050A (ko)	1999-01-25	올레핀 중합 촉매로서의 아자보롤리닐 금속 착화합물
JP2004527608A (ja)	2004-09-09	オレフィン重合触媒成分及び触媒システム、並びにそのような触媒システムを用いた重合プロセス
US6060568A (en)	2000-05-09	Carbene transition metal catalysts
CA2298772A1 (fr)	1999-02-04	Procede permettant de produire des polymeres et des elastomeres stereoreguliers d'alpha.-olefines et nouveaux catalyseurs a utiliser avec ledit procede
US6268448B1 (en)	2001-07-31	Iminophosphonamide complexes for olefin
EP0672676B1 (fr)	2000-10-11	Catalyseurs de polymerisation
US6114270A (en)	2000-09-05	Polymerization-stable anionic ancillary ligand containing alkylimido catalysts and method of using the same
US20030166454A1 (en)	2003-09-04	Heterocyclic-amide catalyst compositions for the polymerization of olefins
EP1997834A1 (fr)	2008-12-03	Catalyseurs
US6696532B2 (en)	2004-02-24	Phosphinimine methanide transition metal catalysts
ES2217104T3 (es)	2004-11-01	Catalizadores de la polimerizacion de olefinas.
EP1716188A1 (fr)	2006-11-02	Clathrochelates utilises comme composants d'un catalyseur de polymerisation d'olefines
KR20000026438A (ko)	2000-05-15	폴리에틸렌 제조용 메탈로센 촉매 및 이를 이용한 폴리에틸렌의제조방법
AU643237C (en)	1999-03-04	Monocyclopentadienyl transition metal olefin polymerization catalysts
KR19990066000A (ko)	1999-08-16	올레핀 중합용 촉매 및 이를 이용한 올레핀의중합방법
US20020147287A1 (en)	2002-10-10	Transition metal donor complexes and olefin polymerization process
Pyridine—Alkoxide	1998	plexes of Tin (II), Gallium (HI), and Indium (III). Syntheses of [(ME) 2ATI] 2GaI and [(Me) 2AT1] 2InCl Using the T in (III)